Glutaryl-7-aminocephalosporanic acid

Base Information

• Chemical Name: Glutaryl-7-aminocephalosporanic acid
• CAS No.: 27920-90-7
• Molecular Formula: C15H18 N2 O8 S
• Molecular Weight: 386.383
• DSSTox Substance ID: DTXSID40182197
• Nikkaji Number: J431.584G
• Wikidata: Q27120425
• Metabolomics Workbench ID: 56419
• Mol file: 27920-90-7.mol

Synonyms:Gl-7-ACA;glutaryl-7-ACA;glutaryl-7-aminocephalosporanic acid

Chemical Property of Glutaryl-7-aminocephalosporanic acid

Chemical Property:

• Vapor Pressure: 2.42E-28mmHg at 25°C
• Boiling Point: 803.3°Cat760mmHg
• PKA: 2.68±0.50(Predicted)
• Flash Point: 439.6°C
• PSA: 175.61000
• Density: 1.56g/cm³
• LogP: -0.12820
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 9
• Exact Mass: 386.07838671
• Heavy Atom Count: 26
• Complexity: 689

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1=C(N2C(C(C2=O)NC(=O)CCCC(=O)O)SC1)C(=O)O
• Isomeric SMILES: CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)CCCC(=O)O)SC1)C(=O)O

Technology Process of Glutaryl-7-aminocephalosporanic acid

There total 4 articles about Glutaryl-7-aminocephalosporanic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 81.0%

cephalosporin C (61-24-5) → 3-acetoxymethyl-7(R)-glutaroylaminoceph-3-em-4-carboxylic acid (27920-90-7) + 7β-(5-carboxy-5-oxopentanamido)cephalosporanic acid (28242-83-3)

Guidance literature:

With oxygen; D-amino acid oxidase (immobilized on glyoxyl agarose); In phosphate buffer; at 25 ℃; for 3.33333h; pH=7.5; Enzymatic reaction;

DOI:10.1002/adsc.200505099

Reference yield:

glutaric anhydride, (108-55-4) + 7-Aminocephalosporanic acid (957-68-6) → 3-acetoxymethyl-7(R)-glutaroylaminoceph-3-em-4-carboxylic acid (27920-90-7)

Guidance literature:

With sodium hydrogencarbonate; In acetone; for 3h;

DOI:10.1016/S0957-4166(03)00171-X

Reference yield:

acetic anhydride (108-24-7) + desacetyl glutaryl 7-aminocephalosporanic acid → 3-acetoxymethyl-7(R)-glutaroylaminoceph-3-em-4-carboxylic acid (27920-90-7)

Guidance literature:

In water; at 0 ℃; Product distribution; dependence on concentrations of substrate, acetic anhydride, pH, and temperature;

DOI:10.7164/antibiotics.47.64

upstream raw materials:

acetic anhydride

glutaric anhydride,

7-Aminocephalosporanic acid

cephalosporin C

Downstream raw materials:

7-Aminocephalosporanic acid

1,5-pentanedioic acid

(6R,7R)-3-Acetoxymethyl-7-(4-carboxybutanamido)ceph-3-em-4-carboxylic acid bis diphenylmethyl ester